


A Boy in a Dress

by migratoryslashfan



Series: The Joys of Scerek [1]
Category: Teen Wolf (TV)
Genre: Alpha Scott, Anal Sex, Bottom Scott, Crossdressing, Crossdressing Kink, Dresses, Dry Sex, Established Relationship, First Time Crossdressing, Future Fic, Kink Discovery, M/M, Mild Painplay, Plot What Plot/Porn Without Plot, Porn with Feelings, Post-Canon, Shopping, Top Derek, Vanilla Kink, Werewolf Pain-Relief Magic
Language: English
Status: Completed
Published: 2015-06-20
Updated: 2015-06-20
Packaged: 2018-04-05 08:59:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,795
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4173843
Author URL: https://archiveofourown.org/users/migratoryslashfan/pseuds/migratoryslashfan
Summary: <blockquote class="userstuff">
              <p>Scott shares a secret with Derek.</p>
            </blockquote>





	A Boy in a Dress

**Author's Note:**

> I don't even know where this came from, but I hope someone likes it! :D
> 
> ETA: If you've ever read Scerek fics before, you probably know better than to read the comments. I've deleted the most triggering sorts of comments and left the rest. Be safe, dear readers!

"I wanna wear a dress," Scott announced.

Derek did a spit-take, exhaling coffee through his nose. He winced at the burn.

"Derek? You okay?"

He shook his head, then nodded. "Yeah, that was just. Surprising."

"You think there's something wrong with a guy in a dress?" Scott asked, but his tone indicated he knew better than to expect Derek to reply with a _yes_ to the question.

"Of course not," Derek said. "It was, well. It was pretty..." He fished around for a word to complete the thought, but he'd already said it had surprised him so there wasn't really anything else to say.

"You're right, I would look pretty," Scott said. And whether he was twisting Derek's statement or he genuinely misinterpreted it, Derek didn't know. "So you're gonna help me pick something out, right?"

"Yes?"

"Good." Scott smiled at him.

\----------

"There are so many to pick from."

Scott wandered the department store's racks of clothing - in the women's section - while Derek shuffled behind him. He wasn't sure how to help a boy pick out a dress to wear, but he definitely wanted to see the end result.

"This feels really weird," Derek said, noticing an elderly lady side-eying the pair of them.

"Do you want to go look at something else?" Scott asked, unable to suppress the disappointment in his voice. "I can look on my own."

Derek appreciated the offer, but he shook his head, taking Scott's hand. "I don't want to look at anything else. I want to help my boyfriend find a dress he likes."

"You're kind of a sap, you know that?" Scott was grinning all the same.

"I'd bet money you like me that way."

"Come on," Scott said, leading Derek along. "I don't know where to start. I don't know my size. I don't even know what I like."

"Well," Derek started, plucking a dress from the nearest rack. "Strapless is probably out."

"Why?"

Derek put the dress back and made a cupping motion in front of his chest. "Nothing to hold it up."

"I've seen flat-chested women in strapless dresses."

"Do you want to try it?"

Scott shrugged. "Gotta start somewhere, right?"

Derek handed the dress over. "Size 10 seems to be in the middle."

"Size 10? What does that even mean? Are there waist measurements I can look at or something?"

"I don't think so," Derek replied.

Scott made a frustrated sound and headed for the nearest dressing room. "I hope they don't tell me I can't go in."

"They may send you to the men's department."

"That'd be fine, I guess."

It ended up not mattering anyway, as Scott and Derek discovered the dressing room area to be empty. Scott jumped into a room and spent a good minute in there before coming out in his own clothes, dress on the hanger.

"This one's too big," he said. "But the next size down should work."

"So now you have a framework for sizing," Derek pointed out. "While you get that one to try on...?"

"Yes, please!" Scott replied, reading his mind.

They split up, each going to retrieve something for Scott to try on. Scott found success with the size 8 strapless dress, but Derek had been right about not having anything to hold it up. Even though it fit snug around his waist, there was a thin gap between the top of the dress and his chest, and he thought it looked funny, so he went to find something else while he waited for Derek to return.

Returning to the dressing room with two items in hand, Scott hung them up side by side. Derek had picked out a white sleeveless [A-line dress](http://www1.macys.com/shop/product/guess-perforated-a-line-dress?ID=2154186&CategoryID=5449&LinkType=#fn=SPECIAL_OCCASIONS%3DDaytime%26sp%3D1%26spc%3D515%26ruleId%3D%26slotId%3D10) with a flaired skirt and small cut-out window beneath the collar on both the front and the back. Scott selected a long [asymmetrical dress](http://www1.macys.com/shop/product/american-rag-printed-asymmetrical-hem-dress?ID=2292074&CategoryID=5449&LinkType=#fn=SPECIAL_OCCASIONS%3DDaytime%26sp%3D1%26spc%3D515%26ruleId%3D%26slotId%3D15) with a brown and green geometric pattern and an empire waistline. He thought that might hide the fact that he had no hips to flair the dress on his own, and he realized Derek's choice would hide that as well.

Scott started with the white dress. The size was right, and it hit just above his knees. He looked down at his hairy legs and briefly wondered if he should shave them. Then he thought about asking Derek to shave them for him, and he discovered he really liked that idea. So much so that he noticed the dress tenting up over his crotch.

"Shit," he mumbled, willing his dick to calm down.

"Everything okay?" Derek asked. Then, in a softer voice, he asked, "Can I see?"

Scott swallowed, the air thick as it entered his lungs. Then he turned to open the dressing room door and noticed his hand was shaking. _What the hell?_ He'd been so gung-ho about this just a few minutes ago, and now he was nervous.

He slid the lock sideways and opened the door, eyebrows raised as he waited for Derek's reaction.

Derek said nothing for a second, just took in the sight of Scott in the dress, eyes moving up and down his body. He let out a sharp breath and leaned away, his back meeting the wall.

"Holy shit," Derek said. "You look..."

"Ridiculous?"

"Sexy," Derek corrected him.

"Really? You're not just saying that?"

Derek cleared his throat and lowered his voice, despite the fact they were alone. "If only we weren't in public right now..."

Scott felt himself blush, and he smiled. "I'll try the other one then."

"Please do," Derek replied.

Scott locked the door again and put his head against the back of it, his grin growing out of control. Then he stepped out of this dress and put on the next one.

When he opened the door again, Derek's first response was to bite his bottom lip, taking in the new sight. "I like that one, too."

"This one's comfortable," Scott said. "They both are. But this one feels like something you could lounge in. Which one do you think...?"

"Why not both?" Derek asked.

Scott checked the tag on the dress he was wearing. "I don't think I can afford both. I probably shouldn't even buy one."

"Why don't I pick one and buy it for you?" Derek suggested, inching closer to the dressing room doorway.

Scott tipped his head a little and let Derek lean in to kiss him.

"Call it a late birthday present," Derek added when they parted.

"That would work," Scott said, slightly breathless.

"Good. Change out of this and hand them both to me. Then we can go back to my place and you can find out which one I liked."

Scott could feel the lasciviousness in his own grin. He shut the door and quickly shimmied out of the dress, handing both articles over the stall door to Derek, and then he pulled his own clothes back on before heading out.

\----------

Scott found himself eagerly anticipating the reveal of which dress Derek picked, bouncing his leg a little on the drive back to the loft. Every couple of minutes or so, he'd glance back to the bag in the backseat, and every time he felt Derek's eyes shift from the road enough to watch him.

"So what do you wanna do once I put it on?" Scott asked. He felt Derek's SUV speed up a little and he laughed.

"I'll let you use your imagination for now," Derek said, "because I'd rather show you."

"What's the speed limit on this road?" Scott asked, palming his crotch a little to ease the growing discomfort there.

Derek chuckled, and sped up just a little more.

\----------

They raced each other to the top of the stairs, Derek holding the bag to keep Scott from peeking before they got inside. They were panting, though not out of breath, as Derek slid the loft door open. Before he could hand the bag over, Scott pushed Derek back against the wall and kissed him, exploring his mouth a little before pulling back.

"Tease," Derek said. He slid the loft's door shut and pushed the bag into Scott's hands. "Go put it on."

Scott's dick gave another jump in his pants at the command. It didn't matter that he was the alpha of the pack; when he and Derek were alone, he rarely held the reigns in their relationship, and he liked it that way.

Dropping the bag onto the bed, Scott turned and watched Derek watch him, pulling off his shirt, then his boots and socks, their eyes locked the whole time.

When he started on his belt, Derek walked over, unable to stop himself as he helped pull the belt from the loops of Scott's jeans. Then he pushed Scott back onto the bed and straddled his thighs briefly as he undid the button and pulled the zipper down. As he inched back toward the foot of the bed, he took Scott's jeans with him, leaving him nearly naked in his boxer briefs while Derek was still fully clothed.

Scott left his erection alone to sit up and open the bag. Then he gasped.

Both dresses were inside.

"I thought you were gonna pick one!"

"I did," Derek said. "And then I picked another."

"Which one should I wear first?"

"That's up to you," Derek said. "This was something you wanted. I'm just along for the - very sexy - ride."

Scott frowned, but he was neither sad nor angry. He couldn't believe Derek sometimes. He knew the guy had money, but still. This was a pretty frivolous purchase he'd made just for Scott to have a dress to play around in at home.

Since he still didn't know which one he liked best, he reached in blindly and pulled out the first one he touched.

It was the white dress. Fitting, he thought, that it would be the one that Derek picked initially. He stood up and put on the dress. And then he waited.

Derek circled him, stopped, spun Scott around to get a good, full look at him. He knelt down, running a hand up Scott's calf, lightly moving the hair and causing Scott to get goosebumps from the touch. He rounded Scott's calf to his shin and stroked fingertips downward, zigzagging to tease the hair on the front of Scott's leg.

Remembering his earlier thought, Scott shivered. He'd suggest shaving later; right now, Derek seemed to be having more fun with him having hair.

Derek's hand traveled further up as he stood, his fingers dipping under the lower hem of Scott's boxer briefs, stroking the front of Scott's thigh.

Scott heard himself moan, and Derek's hand moved further up as if encouraged by the sound, his index finger circling the tip of Scott's leaking cock where it was trapped against his thigh.

Reaching up Scott's skirt with his other hand, Derek tugged Scott's underwear down to his ankles. The alpha stepped out of them as soon as they hit the floor, and Derek tossed them aside.

Then Derek circled Scott until he was facing him. Leaning close, Derek nuzzled Scott's cheek, his hands pulling him in by the shoulders. He ran his hands all over Scott wherever the dress covered him, exploring as if they'd never touched each other so intimately before this moment. From Scott's shoulders, Derek caressed down over his chest, cupping his hips, up around his back, Scott hanging on to Derek's arms the whole time, trying not to sway too much on his feet. Derek finally kissed him then, hands going down Scott's thighs and under his skirt once more.

He pushed the skirt of the dress up Scott's thighs, and when he got to the boy's hips again, he let the skirt fall back down, cupping Scott's erection through the cotton. He held his palm there, warmth against heat, as he continued to kiss Scott, his mouth soon roaming down the younger man's neck and over the fabric covering his clavicle. When he moved lower, to the window cutout over Scott's chest, Derek's tongue darted out for a taste of the boy's copper skin.

"Holy shit," Scott moaned softly, feeling himself leak through the dress, wetting Derek's palm.

Derek paused, reaching around both of his thighs to hoist him up, wrapping Scott's legs around his waist. The skirt poofed upward and Scott's crotch was naked against Derek's clothes. He felt the cool metal of Derek's belt against his balls and couldn't help but grind against it.

"Just a second..." Derek whispered. "Hold on."

He skipped the bed in favor of the wall, backing Scott against it, holding him up with one hand while he undid his belt with the other. All the while, Scott kissed him, or nibbled at his earlobe, or nuzzled his throat, eager to get closer to Derek than his beta would allow. Derek was too slow sometimes; or maybe Scott was just too horny.

Derek freed himself from his pants and lined himself up with Scott's entrance, teasing him with the tip of his cock.

"Do it," Scott moaned.

Derek shook his head. "I haven't prepped you yet."

"Don't care," Scott said, grinding again, this time pulling a groan from Derek as he ran his crotch over Derek's cock.

"Shit, Scott," Derek whimpered. This time he lined himself up properly, inching into Scott with only his own pre-come to slick him.

Scott bit down on a groan, his teeth against Derek's skin as he tried to relax enough for Derek to continue.

"Scott..."

Pushing further, Derek was halfway inside him before he stopped again.

"I can handle it," Scott said, panting heavily. "Please... Fill me up, Derek."

Dirty talk was Derek's weakness, and Scott knew it. He didn't care for it much himself, but when he wanted to encourage his lover to keep going, he knew what he needed to say.

With a hand on Scott's face and another around his waist, Derek buried himself in the boy, kissing him through the discomfort, his veins blackening in one hand as he siphoned off the pain. Scott would chide him for that later, but he couldn't help it; he didn't like causing Scott any pain, even if he said he could handle it. He'd never said he _wanted_ it, and that made all the difference.

Derek fucked Scott against the wall, keeping him aloft as he thrusted. Soon after, Scott shuddered through his orgasm, clenching around Derek's cock as he spilled between their bodies. He gritted through the pain as Derek moved inside him, and then Derek came, filling him up just like he'd asked.

They stayed that way a good long moment, both panting heavily as Derek still held Scott, holding himself up with one hand on the wall beside Scott's head.

"That was..." Derek started.

"...amazing," Scott finished.

"Yeah. That."

Scott laughed. Derek managed to get them both to the bed, where they collapsed like dead weight.

"You okay?" Derek asked. He lazily rubbed a hand on the boy, his knuckles dragging over the inside of Scott's forearm.

"I'm good. You?"

"Perfect," Derek hummed.

"You took the pain."

Derek harrumphed. "I knew you'd say something about that."

"I told you, I can handle it," Scott protested.

"I don't want you to handle it," Derek said. "I don't want you in pain."

Scott pulled himself up, throwing a leg over Derek's body and laying against his chest. "And I don't want you in pain either. Especially not my pain."

"Do you like it?" Derek asked. Scott had never asked for it, but maybe that's because he didn't know he could.

"Sometimes," Scott mumbled, as though ashamed to admit to it.

"You could've said so," Derek replied. "Next time, I'll know. If you want to feel it, I won't take it away."

Scott raised himself enough to meet Derek's eyes. "You don't think it's weird?"

"I don't think anything you like or want is weird," Derek said. He plucked at the dress, tugging a finger under the collar. "I love all of you, Scott."

Scott blushed, ducked and buried his face against Derek's chest. "I love all of you, too," he mumbled on top of him.

Derek chuckled.

Raising his head again, Scott smiled bashfully. "I like my dress, Derek. Thank you."

"I'm glad." Derek slid his hand down Scott's side, along his waist and over his thigh, playing at the hem of the skirt. He lifted it, hand smoothing over Scott's ass, then pulled it back into place. "I like it, too," he admitted.

"I knew you would," Scott said. "I'll wear the other one tomorrow night?"

Derek grinned. "Sounds like a plan."

He let his head fall back onto Derek's chest and let out a contented sigh, knowing there would likely be other dresses in his future.

Scott couldn't wait.


End file.
